Cultural Vacations

Val d’Orcia: Tuscany’s Wine Country Retreat

Pienza, Montalcino, Montepulciano and Siena
4 Days, 3 Nights

Overview

Duration

4 Days, 3 Nights

Group Size

1-6

Destination

Val d'Orcia

Vacation Type

Cultural Vacations

Pick Up

Florence or Bologna airports or Montepulciano railway station

Spend 4 unforgettable days in Val d’Orcia — the rolling hills of southern Tuscany you’ve seen in movies, wine labels, and postcards. This region is quiet, authentic, and rich with beauty.

Walk historic streets in Pienza, Montepulciano, Montalcino, and Siena. Taste Brunello, Vino Nobile, award-winning Tuscan olive oils, and local pecorino cheese — directly where they are made. Surrounded by sweeping countryside and medieval towns, this is Tuscany at its most timeless.

Map of Cultural Vacation Val D'Orcia

Itinerary

You’ll travel into the heart of southern Tuscany for a private guided 3-night stay filled with wine tastings, scenic hill towns, breathtaking viewpoints, artisan shops, and authentic local food.

Everything is arranged for you — no driving, no logistics, no stress — just pure enjoyment.

A complete, detailed day-by-day itinerary will be customized around your interests and finalized based on seasonality and opening schedules.

Sample Itinerary

  • Day 1: Check-in and enjoy lunch at a local restaurant in Pienza. Afternoon walk to explore. Aperitif and dinner at a local restaurant.
  • Day 2: Visit Montepulciano for a guided wine tasting and lunch at a local restaurant. Stroll and explore local shops.
  • Day 3: Breakfast. Visit Montalcino for a guided wine tasting and lunch at a local restaurant. Stroll and explore local shops. Dinner at a local restaurant.
  • Day 4: Breakfast. Check out, enjoy lunch at a local restaurant in Siena and explore the famous piazza and shops. Afternoon drop off in Florence.

Accommodations

In Val d’Orcia, you’ll stay in a charming countryside hotel with panoramic views of the Tuscan hills. Expect peaceful surroundings, relaxed elegance, warm hospitality — and evenings that feel like a painting as the sun sets over the valley. It’s the perfect place to unwind after exploring one of Italy’s most beloved landscapes.

Dates & Pricing

This all-inclusive cultural vacation is available year-round, based on availability. Pricing is listed per person and includes accommodations, meals, wines, transportation, cooking classes and all guided touring.

Private: 2-6 persons

$3,950
per person

What's Included

  • Morning pick-up at Montepulciano railway station or Florence or Bologna airports
  • All transportation during your culinary course vacation
  • 3 nights accommodation in Val D’Orcia
  • Market visits, wine and food tastings, tickets and tours
  • Return transportation to the train station or airport on the morning of the last day

Vacation Upgrades

Want to add hands-on Italian cooking classes before or after Val d’Orcia?

Turn this cultural vacation into a full Italian culinary experience by upgrading to include 4 immersive cooking days with Chef Stefano on Monte Fumaiolo. We’ll customize everything for you — simply ask.

You can add on additional 4-day destinations like Florence, Orvieto, Bologna or Venice. Tell us where you’ve always dreamed of going — and we’ll design a custom extension to your itinerary.

Plan your Italy Culinary Vacation today!

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